#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/32/4023296.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4023296
loop_
_publ_author_name
'Tsuyoshi Hosokawa'
'Akemi Matsumura'
'Toshimasa Katagiri'
'Kenji Uneyama'
_publ_section_title
;
 One-Pot Synthesis of 3-Fluoro-4-(trifluoromethyl)quinolines
 from Pentafluoropropen-2-ol and Their Molecular Modification
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1468
_journal_page_last               1474
_journal_paper_doi               10.1021/jo702568z
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C17 H11 F4 N O '
_chemical_formula_sum            'C17 H11 F4 N O'
_chemical_formula_weight         321.27
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_audit_creation_date             'Thu May 31 16:52:10 2007'
_audit_creation_method           'by teXsan'
_cell_angle_alpha                90
_cell_angle_beta                 107.867(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4092(6)
_cell_length_b                   18.552(2)
_cell_length_c                   10.841(1)
_cell_measurement_reflns_used    10117
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.3
_cell_volume                     1418.3(3)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SIR97
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.9412
_diffrn_measured_fraction_theta_max 0.9412
_diffrn_measurement_device_type  'Rigaku RAXIS-IV Imaging Plate'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.020
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10627
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.42
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.198
_refine_ls_hydrogen_treatment    refU
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2118
_refine_ls_R_factor_gt           0.0788
_refine_ls_shift/su_max          0.0059
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(Fo) + 0.00990|Fo|²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1189
_reflns_number_gt                2118
_reflns_number_total             3056
_reflns_threshold_expression     F²>5.0σ(F²)
_cod_data_source_file            jo702568z-File001.cif
_cod_data_source_block           katagiri118
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_original_formula_sum        'C17 H11 F4 N O '
_cod_database_code               4023296
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,1/2+y,-z
-x,-y,-z
1/2+x,1/2-y,z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F(1) F 0.9455(3) 0.19740(9) 0.5778(2) 0.0715(6) Uani 1.00 d . . .
F(5) F 0.8454(5) 0.2081(1) 0.3400(2) 0.128(1) Uani 1.00 d . . .
F(6) F 0.8351(4) 0.1119(1) 0.2386(2) 0.0994(8) Uani 1.00 d . . .
F(7) F 0.5830(4) 0.1520(2) 0.2580(2) 0.1055(8) Uani 1.00 d . . .
O(1) O 0.5013(3) -0.1203(1) 0.2176(2) 0.0654(6) Uani 1.00 d . . .
N(1) N 0.8430(3) 0.0227(1) 0.6739(2) 0.0474(5) Uani 1.00 d . . .
C(1) C 0.7947(3) 0.1008(1) 0.4444(2) 0.0497(6) Uani 1.00 d . . .
C(2) C 0.7332(3) 0.0278(1) 0.4363(2) 0.0457(6) Uani 1.00 d . . .
C(3) C 0.8948(3) 0.0908(1) 0.6803(2) 0.0471(6) Uani 1.00 d . . .
C(4) C 0.7665(3) -0.0089(1) 0.5564(2) 0.0469(6) Uani 1.00 d . . .
C(5) C 0.6300(4) -0.1175(1) 0.4422(3) 0.0559(7) Uani 1.00 d . . .
C(6) C 0.5919(4) -0.0804(1) 0.3228(3) 0.0519(6) Uani 1.00 d . . .
C(7) C 0.9714(4) 0.1234(1) 0.8114(3) 0.0523(7) Uani 1.00 d . . .
C(8) C 0.6432(3) -0.0093(1) 0.3198(2) 0.0512(7) Uani 1.00 d . . .
C(9) C 1.0705(4) 0.0794(2) 0.9143(3) 0.0584(7) Uani 1.00 d . . .
C(10) C 0.7660(5) 0.1456(2) 0.3228(3) 0.0655(8) Uani 1.00 d . . .
C(11) C 0.9333(5) 0.1946(2) 0.8370(3) 0.0636(8) Uani 1.00 d . . .
C(15) C 0.9958(6) 0.2197(2) 0.9643(3) 0.076(1) Uani 1.00 d . . .
C(16) C 0.4279(4) -0.0845(2) 0.0963(3) 0.0692(9) Uani 1.00 d . . .
C(17) C 1.0972(5) 0.1755(2) 1.0650(3) 0.0748(10) Uani 1.00 d . . .
C(18) C 1.1332(5) 0.1061(2) 1.0396(3) 0.0684(9) Uani 1.00 d . . .
C(19) C 0.8763(4) 0.1297(1) 0.5648(3) 0.0517(7) Uani 1.00 d . . .
C(20) C 0.7137(4) -0.0825(1) 0.5552(3) 0.0533(7) Uani 1.00 d . . .
H(1) H 0.5976 -0.1674 0.4438 0.074(9) Uiso 1.00 calc . . .
H(2) H 0.6178 0.0152 0.2391 0.068(8) Uiso 1.00 calc . . .
H(3) H 1.0944 0.0303 0.8974 0.068(8) Uiso 1.00 calc . . .
H(4) H 0.8661 0.2250 0.7673 0.071(9) Uiso 1.00 calc . . .
H(5) H 0.9713 0.2682 0.9836 0.10(1) Uiso 1.00 calc . . .
H(6) H 1.1424 0.1939 1.1506 0.09(1) Uiso 1.00 calc . . .
H(7) H 1.2016 0.0742 1.1080 0.10(1) Uiso 1.00 calc . . .
H(8) H 0.7363 -0.1077 0.6369 0.056(7) Uiso 1.00 calc . . .
H(9) H 0.5284 -0.0611 0.0752 0.11(1) Uiso 1.00 calc . . .
H(10) H 0.3694 -0.1186 0.0315 0.11(1) Uiso 1.00 calc . . .
H(11) H 0.3371 -0.0497 0.1030 0.074(9) Uiso 1.00 calc . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
F F 0.017 0.010
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
N N 0.006 0.003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
O O 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(6) O(1) C(16) 118.3(2) . . . yes
C(3) N(1) C(4) 119.7(2) . . . yes
C(2) C(1) C(10) 120.7(2) . . . yes
C(2) C(1) C(19) 118.1(2) . . . yes
C(10) C(1) C(19) 121.2(2) . . . yes
C(1) C(2) C(4) 115.9(2) . . . yes
C(1) C(2) C(8) 125.0(2) . . . yes
C(4) C(2) C(8) 119.1(2) . . . yes
N(1) C(3) C(7) 117.5(2) . . . yes
N(1) C(3) C(19) 119.7(2) . . . yes
C(7) C(3) C(19) 122.8(2) . . . yes
N(1) C(4) C(2) 123.9(2) . . . yes
N(1) C(4) C(20) 117.3(2) . . . yes
C(2) C(4) C(20) 118.8(2) . . . yes
C(6) C(5) C(20) 120.0(2) . . . yes
O(1) C(6) C(5) 114.4(2) . . . yes
O(1) C(6) C(8) 125.0(2) . . . yes
C(5) C(6) C(8) 120.6(2) . . . yes
C(3) C(7) C(9) 118.6(2) . . . yes
C(3) C(7) C(11) 122.3(2) . . . yes
C(9) C(7) C(11) 118.9(3) . . . yes
C(2) C(8) C(6) 120.3(2) . . . yes
C(7) C(9) C(18) 120.7(3) . . . yes
F(5) C(10) F(6) 105.5(3) . . . yes
F(5) C(10) F(7) 110.0(3) . . . yes
F(5) C(10) C(1) 115.5(3) . . . yes
F(6) C(10) F(7) 103.0(3) . . . yes
F(6) C(10) C(1) 111.0(2) . . . yes
F(7) C(10) C(1) 110.9(2) . . . yes
C(7) C(11) C(15) 119.2(3) . . . yes
C(11) C(15) C(17) 121.0(3) . . . yes
C(15) C(17) C(18) 119.5(3) . . . yes
C(9) C(18) C(17) 120.6(3) . . . yes
F(1) C(19) C(1) 120.5(2) . . . yes
F(1) C(19) C(3) 117.0(2) . . . yes
C(1) C(19) C(3) 122.5(2) . . . yes
C(4) C(20) C(5) 121.1(2) . . . yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F(1) C(19) 1.347(3) . . yes
F(5) C(10) 1.288(4) . . yes
F(6) C(10) 1.331(4) . . yes
F(7) C(10) 1.327(4) . . yes
O(1) C(6) 1.353(3) . . yes
O(1) C(16) 1.423(4) . . yes
N(1) C(3) 1.316(3) . . yes
N(1) C(4) 1.358(3) . . yes
C(1) C(2) 1.424(3) . . yes
C(1) C(10) 1.517(4) . . yes
C(1) C(19) 1.368(4) . . yes
C(2) C(4) 1.422(3) . . yes
C(2) C(8) 1.413(3) . . yes
C(3) C(7) 1.488(3) . . yes
C(3) C(19) 1.416(3) . . yes
C(4) C(20) 1.420(3) . . yes
C(5) C(6) 1.416(4) . . yes
C(5) C(20) 1.357(4) . . yes
C(6) C(8) 1.375(4) . . yes
C(7) C(9) 1.396(4) . . yes
C(7) C(11) 1.395(4) . . yes
C(9) C(18) 1.385(4) . . yes
C(11) C(15) 1.395(4) . . yes
C(15) C(17) 1.388(6) . . yes
C(17) C(18) 1.361(5) . . yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
F(1) C(5) 3.475(3) . 2_656 ?
F(1) C(5) 3.543(3) . 3_756 ?
F(5) F(7) 3.404(4) . 4_555 ?
F(6) C(17) 3.309(4) . 1_554 ?
F(6) N(1) 3.381(3) . 3_756 ?
F(6) C(20) 3.447(4) . 3_756 ?
F(6) C(18) 3.531(4) . 1_554 ?
F(6) C(16) 3.591(4) . 3_655 ?
F(7) C(18) 3.549(4) . 1_454 ?
F(7) C(17) 3.592(5) . 1_454 ?
O(1) C(11) 3.383(4) . 3_656 ?
O(1) C(7) 3.420(3) . 3_656 ?
O(1) C(3) 3.483(3) . 3_656 ?
O(1) C(11) 3.544(4) . 2_646 ?
O(1) C(15) 3.567(4) . 2_646 ?
N(1) C(6) 3.406(3) . 3_656 ?
C(2) C(20) 3.491(3) . 3_656 ?
C(7) C(16) 3.478(4) . 3_656 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F(1) C(19) C(1) C(2) 176.7(2) . . . . yes
F(1) C(19) C(1) C(10) -4.7(4) . . . . yes
F(1) C(19) C(3) N(1) -174.9(2) . . . . yes
F(1) C(19) C(3) C(7) 5.0(4) . . . . yes
F(5) C(10) C(1) C(2) -172.5(3) . . . . yes
F(5) C(10) C(1) C(19) 8.9(5) . . . . yes
F(6) C(10) C(1) C(2) -52.5(4) . . . . yes
F(6) C(10) C(1) C(19) 128.9(3) . . . . yes
F(7) C(10) C(1) C(2) 61.4(3) . . . . yes
F(7) C(10) C(1) C(19) -117.2(3) . . . . yes
O(1) C(6) C(5) C(20) -177.4(2) . . . . yes
O(1) C(6) C(8) C(2) 178.3(2) . . . . yes
N(1) C(3) C(7) C(9) 31.2(3) . . . . yes
N(1) C(3) C(7) C(11) -143.0(3) . . . . yes
N(1) C(3) C(19) C(1) 4.3(4) . . . . yes
N(1) C(4) C(2) C(1) 3.2(3) . . . . yes
N(1) C(4) C(2) C(8) -176.5(2) . . . . yes
N(1) C(4) C(20) C(5) 177.6(2) . . . . yes
C(1) C(2) C(4) C(20) -178.2(2) . . . . yes
C(1) C(2) C(8) C(6) 179.0(2) . . . . yes
C(1) C(19) C(3) C(7) -175.8(2) . . . . yes
C(2) C(1) C(19) C(3) -2.5(4) . . . . yes
C(2) C(4) N(1) C(3) -1.6(4) . . . . yes
C(2) C(4) C(20) C(5) -1.0(4) . . . . yes
C(2) C(8) C(6) C(5) -0.6(4) . . . . yes
C(3) N(1) C(4) C(20) 179.9(2) . . . . yes
C(3) C(7) C(9) C(18) -175.5(2) . . . . yes
C(3) C(7) C(11) C(15) 174.4(3) . . . . yes
C(3) C(19) C(1) C(10) 176.1(2) . . . . yes
C(4) N(1) C(3) C(7) 177.9(2) . . . . yes
C(4) N(1) C(3) C(19) -2.2(3) . . . . yes
C(4) C(2) C(1) C(10) -179.7(2) . . . . yes
C(4) C(2) C(1) C(19) -1.1(3) . . . . yes
C(4) C(2) C(8) C(6) -1.2(4) . . . . yes
C(4) C(20) C(5) C(6) -0.8(4) . . . . yes
C(5) C(6) O(1) C(16) 169.3(2) . . . . yes
C(7) C(9) C(18) C(17) 0.8(5) . . . . yes
C(7) C(11) C(15) C(17) 0.9(5) . . . . yes
C(8) C(2) C(1) C(10) 0.0(4) . . . . yes
C(8) C(2) C(1) C(19) 178.6(2) . . . . yes
C(8) C(2) C(4) C(20) 2.0(4) . . . . yes
C(8) C(6) O(1) C(16) -9.7(4) . . . . yes
C(8) C(6) C(5) C(20) 1.6(4) . . . . yes
C(9) C(7) C(3) C(19) -148.7(3) . . . . yes
C(9) C(7) C(11) C(15) 0.3(4) . . . . yes
C(9) C(18) C(17) C(15) 0.4(5) . . . . yes
C(11) C(7) C(3) C(19) 37.1(3) . . . . yes
C(11) C(7) C(9) C(18) -1.2(4) . . . . yes
C(11) C(15) C(17) C(18) -1.3(5) . . . . yes
C(11) C(15) C(17) C(18) -1.3(5) . . . . yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658642
